5-溴-N-[(4-甲氧基苯基)甲基]呋喃-2-甲酰胺 | 545438-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-溴-N-[(4-甲氧基苯基)甲基]呋喃-2-甲酰胺
• 英文名称: 5-bromofuran-2-carboxylic acid 4-methoxybenzylamide
• 英文别名: 5-bromo-furan-2-carboxylic acid 4-methoxy-benzylamide；5-bromo-N-[(4-methoxyphenyl)methyl]furan-2-carboxamide
• CAS: 545438-21-9
• 化学式: C₁₃H₁₂BrNO₃
• mdl: MFCD03391498
• 分子量: 310.147
• InChiKey: FFVGCUVFUWKYAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  447.3±45.0 °C(Predicted)
• 密度：
  1.452±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-硝基-2-糠酰氯 、 5-溴-N-[(4-甲氧基苯基)甲基]呋喃-2-甲酰胺 以 二氯甲烷 、 三乙胺 为溶剂， 以83%的产率得到N-(4-morpholinylphenyl)-5-nitrofuran-2-carboxamide
  参考文献：
  名称：

  Heterocyclic amides with anti-tuberculosis activity

  摘要：

  具有一般结构的化合物：其中A从氧、硫和NR15组成的群体中选择，R15从H、烷基、芳基、取代烷基和取代芳基组成的群体中选择；B、D和E分别独立地从CH、氮、硫和氧组成的群体中选择；R1从硝基、卤素、烷基酯、芳基硫醚、芳基亚砜、芳基砜基和磺酸中选择；t为1到3的整数；X为取代酰胺，并且使用这些新化合物治疗由微生物引起的感染的方法，包括结核分枝杆菌。

  公开号：

  US20050222408A1
• 作为产物：
  描述：

  5-溴-2-糠酸 、 4-甲氧基苄胺 在 4-二甲氨基吡啶 、 oligomeric alkyl cyclohexylcarbodiimide 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到5-溴-N-[(4-甲氧基苯基)甲基]呋喃-2-甲酰胺
  参考文献：
  名称：

  高负荷，可溶性寡聚碳二亚胺：合成及其在偶联反应中的应用

  摘要：

  描述了通过ROM聚合由市售的起始原料容易地制备高负荷的可溶性低聚烷基环己基碳二亚胺（OACC）试剂的方法。该试剂被用作偶联试剂，用于将羧酸（脂族和芳族）与各种醇（脂族伯，仲和苄基），硫醇，酚和胺（脂族伯，仲，分别是苄基和芳族/苯胺）。偶合事件发生后，用适当的溶剂（Et 2 O，MeOH或EtOAc）沉淀，然后通过SPE过滤，可提供具有极佳收率和纯度的产物。

  DOI：

  10.1021/jo048870c

文献信息

• [EN] HETEROCYCLIC AMIDES WITH ANTI-TUBERCULOSIS ACTIVITY<br/>[FR] AMIDES HETEROCYCLIQUES A ACTIVITE ANTI-TUBERCULINIQUE
  申请人：UNIV TENNESSEE RES FOUNDATION

  公开号：WO2005007625A3

  公开（公告）日：2005-12-29
• Synthesis and Evaluation of Nitrofuranylamides as Novel Antituberculosis Agents
  作者：Rajendra P. Tangallapally、Raghunandan Yendapally、Robin E. Lee、Kirk Hevener、Victoria C. Jones、Anne J. M. Lenaerts、Michael R. McNeil、Yuehong Wang、Scott Franzblau、Richard E. Lee

  DOI：10.1021/jm049972y

  日期：2004.10.1

  In an effort to develop new and more potent therapies to treat tuberculosis, a library of compounds was screened for M. tuberculosis UDP-Gal mutase inhibition. Nitrofuranylamide 1 was identified as a hit in this screen, possessing good antituberculosis activity. This paper describes the synthesis and evaluation of an expanded set of nitrofaranylamides. We have discovered a number of nitrofaranylamides with submicromolar M. tuberculosis MIC values and acceptable therapeutic indexes. The MIC activity did not correlate with UDP-Gal mutase inhibition, suggesting an alternative primary cellular target was responsible for the antituberculosis activity. The compounds were only active against mycobacteria of the tuberculosis complex. On the basis of these results, four compounds were selected for in vivo testing in a mouse model of tuberculosis infection, and of these compounds one showed significant antituberculosis activity.
• High-Load, Soluble Oligomeric Carbodiimide:  Synthesis and Application in Coupling Reactions
  作者：Mianji Zhang、Punitha Vedantham、Daniel L. Flynn、Paul R. Hanson

  DOI：10.1021/jo048870c

  日期：2004.11.1

  A facile preparation of a high-load, soluble oligomeric alkyl cyclohexylcarbodiimide (OACC) reagent via ROM polymerization from commercially available starting materials is described. This reagent is exploited as a coupling reagent for esterification, amidation, and dehydration of carboxylic acids (aliphatic and aromatic) with an assortment of alcohols (aliphatic primary, secondary, and benzylic),

  描述了通过ROM聚合由市售的起始原料容易地制备高负荷的可溶性低聚烷基环己基碳二亚胺（OACC）试剂的方法。该试剂被用作偶联试剂，用于将羧酸（脂族和芳族）与各种醇（脂族伯，仲和苄基），硫醇，酚和胺（脂族伯，仲，分别是苄基和芳族/苯胺）。偶合事件发生后，用适当的溶剂（Et 2 O，MeOH或EtOAc）沉淀，然后通过SPE过滤，可提供具有极佳收率和纯度的产物。
• Heterocyclic amides with anti-tuberculosis activity
  申请人：Lee E. Richard

  公开号：US20050222408A1

  公开（公告）日：2005-10-06

  Compounds having the general structure: wherein A is selected from the group consisting of oxygen, sulfur, and NR 15 , and R 15 is selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; B,D, and E are each independently selected from the group consisting of CH, nitrogen, sulfur and oxygen; R 1 is selected from the group consisting of nitro, halo, alkyl ester, arylsulfanyl, arylsulfinyl, arylsulfonyl and sulfonic acid; t is an integer from 1 to 3; and X is a substituted amide, and methods of using the novel compounds for treating infections caused by microorganisms, including Mycobacterium tuberculosis.

  具有一般结构的化合物：其中A从氧、硫和NR15组成的群体中选择，R15从H、烷基、芳基、取代烷基和取代芳基组成的群体中选择；B、D和E分别独立地从CH、氮、硫和氧组成的群体中选择；R1从硝基、卤素、烷基酯、芳基硫醚、芳基亚砜、芳基砜基和磺酸中选择；t为1到3的整数；X为取代酰胺，并且使用这些新化合物治疗由微生物引起的感染的方法，包括结核分枝杆菌。